TWI780469B - Dye compound, photosensitive resin composition, photosensitive resin layer, color filter and display device - Google Patents

Abstract

The present specification provides a dye compound, a photosensitive resin composition, a photosensitive resin layer, a color filter, and a display device. The dye compound represented by Chemical Formula 1:

Description

Dye compound, photosensitive resin composition, photosensitive resin layer, color filter, and display device

The present invention relates to a novel dye compound, a photosensitive resin composition containing the compound, a photosensitive resin layer produced using the photosensitive resin composition, a color filter containing the photosensitive resin layer sheet and a display device including the color filter.

Among many types of displays, liquid crystal display devices have advantages in brightness, thinness, low cost, low operating power consumption, and improved adhesion to integrated circuits, and have been more widely used in laptop computers, monitors, and TV screen. The liquid crystal display device comprises: a lower substrate, on which a light-shielding layer, a color filter, and an ITO pixel electrode are formed; and an upper substrate, on which an active circuit part and an ITO pixel electrode are formed, and the active circuit part includes a liquid crystal layer, a film Transistor and capacitor layers. Each image is formed by sequentially stacking a plurality of color filters (generally, formed of three primary colors such as red (R), green (G) and blue (B)) in a predetermined order. A color filter is traditionally formed in a pixel region, and a light shielding layer is disposed on a transparent substrate in a predetermined pattern to form a boundary between pixels.

Color filters are widely used in photographic devices, liquid crystal display devices (LCD), field emission displays (FEL), light emitting displays (LED) and the like, and their The scope of applications is rapidly expanding. Specifically, in recent years, liquid crystal display devices have advantages of light weight, low power, low driving voltage, and the like, and thus have been more diversely used in recent years, and accordingly, color filters are regarded as One of the most important parts to reproduce the color tone of the liquid crystal display device.

Since high color reproducibility, high resolution, distinct contrast ratio, and the like are required due to the nature of the display industry, the importance of color is emphasized among key parts of liquid crystal display devices. Because the pigments currently used for color filters have excellent characteristics (such as heat resistance, light resistance, chemical resistance, and the like), but their solubility is insufficient and thus dispersed and used in a particle state, there are disadvantages, that is, due to Insufficient color contrast and fuzzy shades, the monitor may display poor colors. Because of this disadvantage, the need to use dyes instead of pigments is increasing. Compared with pigments, dyes are sufficiently soluble and facilitate high color rendition.

On the other hand, in order to use a dye for a color filter, the dye should satisfy appropriate conditions of wavelength, absorbance, light transmittance, heat resistance, light resistance, and chemical resistance, and the like. Among red dyes, a xanthene-based compound has a high extinction coefficient and is thus advantageous for coloring, and it also has Has excellent durability and is therefore widely used as a red dye.

However, even if xanthene compounds are used as red dyes, since the high brightness and high durability characteristics of xanthene compounds have not reached a satisfactory level compared with other dyes, attempts have been made to improve xanthene compounds. compound, and thus achieve better brightness and durability.

One example will provide a novel dye compound.

Another embodiment provides a photosensitive resin composition comprising the dye compound.

Another embodiment will provide a photosensitive resin layer produced using the photosensitive resin composition.

Another embodiment will provide a color filter produced using the photosensitive resin composition.

Another embodiment provides a display device including the color filter.

An embodiment provides a dye compound represented by Chemical Formula 1.

In Chemical Formula 1, R ¹ is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group or a combination thereof, R ² , R ⁴ and R ⁵ are independently substituted Substituted or unsubstituted C1 to C20 alkylene, substituted or unsubstituted C3 to C20 cycloalkylene, substituted or unsubstituted C6 to C20 arylylene, substituted or unsubstituted C2 to C20 heteroaryl or a combination thereof, and R ³ is hydrogen, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or Unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C2 to C20 heterocyclic group or a combination thereof.

^R2 and ^R4 can be independently substituted or unsubstituted C1 to C20 alkylene or substituted or unsubstituted C3 to C20 cycloalkylene, and ^R5 can be substituted or unsubstituted C1 to C20 alkylene, substituted or unsubstituted C3 to C20 cycloalkylene, substituted or unsubstituted C6 to C20 arylylene, substituted or unsubstituted C2 to C20 heteroaryl or a combination thereof.

R can be ^a substituted or unsubstituted C6 to C20 aryl group, and R5 can be a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 ^arylylene group, or its combination.

R ¹ may be a compound represented by Chemical Formula 2.

[chemical formula 2]

In Chemical Formula 2, R ^a to R ^e are independently hydrogen or substituted or unsubstituted C1 to C5 alkyl, and "*" represents a point of attachment.

R ⁵ may be a compound represented by Chemical Formula 3.

In Chemical Formula 3, L ^a and L ^b are independently a single bond or a substituted or unsubstituted C1 to C5 alkylene group, and "*" represents a point of attachment.

The compound may be a compound represented by one of Chemical Formula 4-1 to Chemical Formula 4-4.

[chemical formula 4-1]

The compound represented by Chemical Formula 1 may have the maximum absorbance in a wavelength range of 500 nm to 600 nm.

Another embodiment includes a colorant including a red dye, and the red dye provides a photosensitive resin composition including the compound represented by Chemical Formula 1.

The photosensitive resin composition may further include a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

The binder resin may include an acryl-based binder resin, a cardole-based binder resin, or a combination thereof.

The colorant may further contain pigments.

Based on the total amount of the photosensitive resin composition, the photosensitive resin composition may include 1% by weight to 50% by weight of a colorant, 1% by weight to 30% by weight of a binder resin, and 1% by weight to 15% by weight of a photosensitive resin. A polymerizable monomer, 0.01% by weight to 10% by weight of a photopolymerization initiator, and a balance amount of a solvent.

The photosensitive resin composition may further include malonic acid, 3-amino-1,2-propanediol, silane coupling agent containing vinyl or (meth)acryloxy, leveling agent, surfactant, free radical polymerization starter or a combination thereof.

Another embodiment provides a photosensitive resin layer produced using the photosensitive resin composition.

Another embodiment provides a color filter produced by using the photosensitive resin composition.

Another embodiment provides a display device including the color filter.

The compound according to an embodiment has improved solubility in organic solvents and has excellent fluorescence control and spectral uniformity, and a photosensitive resin composition including the compound as a colorant can be produced with improved brightness, heat resistance, and chemical resistance color filters and the like.

Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto and the present invention is defined by the claims of the invention.

In this specification, when no specific definition is otherwise provided, "substituted" means substituted by a substituent selected from the following: halogen (F, Br, Cl or I), hydroxyl, nitro, cyano, amino (NH ₂ , NH(R ²⁰⁰ ) or N(R ²⁰¹ )(R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different, and are independently C1 to C10 alkyl), formamidinyl, hydrazino, hydrazone, Carboxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alicyclic organic group, substituted or unsubstituted Substituted aryl and substituted or unsubstituted heterocyclyl.

In this specification, when no specific definition is otherwise provided, "alkyl" refers to C1 to C20 alkyl, and specifically C1 to C15 alkyl, "cycloalkyl" refers to C3 to C20 cycloalkyl, and Specifically C3 to C18 cycloalkyl, "alkoxy" refers to C1 to C20 alkoxy, and specifically C1 to C18 alkoxy, "aryl" refers to C6 to C20 aryl, and specifically Referring to C6 to C18 aryl, "alkenyl" means C2 to C20 alkenyl, and specifically C2 to C18 alkenyl, and "alkylene" means C1 to C20 alkylene, and specifically C1 to C18 Alkylene, and "aryl" refers to C6 to C20 Arylylene, and specifically C6 to C16 arylylene.

In this specification, when no specific definition is otherwise provided, "(meth)acrylate" means "acrylate" and "methacrylate", and "(meth)acrylic" means "acrylic" and " Methacrylate".

In this specification, when no definition is provided otherwise, "combination" means mixing or copolymerization. In addition, "copolymerization" means block copolymerization to random copolymerization, and "copolymer" means block copolymer to random copolymerization.

In the chemical formulas in this specification, unless a specific definition is provided otherwise, when a chemical bond is not drawn, hydrogen is bonded at a presumably given position.

In this specification, a cardo-based resin refers to a resin including at least one functional group selected from Chemical Formula 6-1 to Chemical Formula 6-11 in the main structure of the resin.

In this specification, when no specific definition is otherwise provided, "*" indicates a point of bonding (connection) to the same or different atoms or chemical formulas.

An embodiment provides a dye compound represented by Chemical Formula 1.

In Chemical Formula 1, R ¹ is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group or a combination thereof, R ² , R ⁴ and R ⁵ are independently substituted Substituted or unsubstituted C1 to C20 alkylene, substituted or unsubstituted C3 to C20 cycloalkylene, substituted or unsubstituted C6 to C20 arylylene, substituted or unsubstituted C2 to C20 heteroaryl or a combination thereof, and R ³ is hydrogen, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or Unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C2 to C20 heterocyclic group or a combination thereof.

A color filter produced by using a pigment-type photosensitive resin composition has limitations in brightness and contrast ratio caused by the particle size of the pigment. In addition, image sensor devices require smaller dispersed particle sizes to form fine patterns. In order to meet the requirements, attempts have been made to obtain a color filter with improved brightness and contrast ratio by introducing a non-particle-forming dye instead of a pigment to prepare a photosensitive resin composition suitable for the dye.

In general, since a photosensitive resin composition including a xanthene compound in which charges are separated has extremely low solubility to an organic solvent such as PGMEA and exhibits deteriorated durability such as heat resistance and chemical resistance, xanthene There are restrictions on the use of tonnane compounds as colorants in photosensitive resin compositions.

However, the compound according to an embodiment, that is, the compound represented by Chemical Formula 1 can improve the solubility to organic solvents, and in addition, because the substituted or unsubstituted C6 to C20 aryl group, the substituted or unsubstituted C2 to C20 heteroaryl or The combination thereof must be bonded to nitrogen atoms (the nitrogen atoms are bonded to the xanthene compound) at both ends of the compound, so the photosensitive resin composition containing the compound can improve the brightness and durability of the color filter, such as heat resistance resistance, chemical resistance, and the like.

In addition, the compound represented by Chemical Formula ¹ has a dimer form linked by a linking group comprising two carbamate groups bonded to both sides of the R group, and thus the The compound has excellent fluorescence control and spectral uniformity, and accordingly, the photosensitive resin composition containing the compound can be used to improve the brightness and contrast ratio of a color filter.

^The R group can be a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylylene group, a substituted or unsubstituted C6 to C20 arylylene group, A substituted or unsubstituted C2 to C20 heteroaryl group or a combination thereof, and ideally a substituted or unsubstituted C6 to C20 arylylene group or a substituted or unsubstituted C2 to C20 heteroaryl group.

R ² and R ⁴ may be independently substituted or unsubstituted ^C1 to C20 alkylene or substituted or unsubstituted C3 to C20 cycloalkylene, and specifically, R may be substituted or unsubstituted Substituted C6 to C20 aryl, for example, C6 to C18 aryl, C6 to C14 aryl or C6 to C10 aryl. When the R ¹ group is an aryl group as described above, it is possible to improve durability, such as brightness, heat resistance, and chemical resistance, of a color filter produced using a photosensitive resin composition including the compound.

R ⁵ may be a substituted or unsubstituted C1 to C20 alkylene group (such as a C1 to C16 alkylene group, such as a C1 to C12 alkylene group) or a substituted or unsubstituted C6 to C20 arylylene group (such as C6 to C14 aryl, such as C6 to C10 aryl) or a combination thereof.

For example, R ¹ may be represented by Chemical Formula 2.

In Chemical Formula 2, R ^a to R ^e are independently hydrogen or substituted or unsubstituted C1 to C5 alkyl groups.

For example, R ⁵ may be represented by Chemical Formula 3.

In Chemical Formula 3, L ^a and L ^b are independently a single bond or a substituted or unsubstituted C1 to C5 alkylene group.

When R ¹ is represented by Chemical Formula 2 and R ⁵ is represented by Chemical Formula 3 at the same time, the durability of the compound represented by Chemical Formula 1 may be greatly improved.

In addition, the compound represented by Chemical Formula 1 includes (meth)acrylate groups at both terminals, and thus, the photosensitive resin composition including the compound can be improved. Solubility in organic solvents. In addition, the compound contains (meth)acrylate groups at both terminals, and thus can undergo a copolymerization reaction with a monomer, and thus form a polymer. For example, the monomer can be an ethylenically unsaturated monomer, and in this case, the polymer can be an acrylic polymer.

For example, ethylenically unsaturated monomers can be aromatic vinyl compounds, unsaturated carboxylate compounds, unsaturated aminoalkyl carboxylate compounds, vinyl carboxylate compounds, unsaturated glycidyl carboxylate compounds , vinyl cyanide compounds, unsaturated amide compounds or combinations thereof.

Ethylenically unsaturated monomers may be, for example: aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, vinylbenzyl methyl ether, and the like; unsaturated carboxylic acid esters Compounds such as (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl acrylate, 2-hydroxyl (meth)acrylate Ethyl esters, 2-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, phenyl (meth)acrylate and the like; unsaturated aminoalkylcarboxylic acids Ester compounds such as 2-aminoethyl (meth)acrylate, 2-dimethylaminoethyl (meth)acrylate, and the like; vinyl carboxylate compounds, such as vinyl acetate, vinyl benzoate, and the like; Unsaturated glycidyl carboxylate compounds such as glycidyl (meth)acrylate and the like; vinyl cyanide compounds such as (meth)acrylonitrile and the like; unsaturated amide compounds such as (methyl) Acrylamide and the like, or combinations thereof.

Acrylic polymer, which is a copolymerization product of a compound represented by Chemical Formula 1 and an ethylenically unsaturated monomer, has excellent heat resistance and handleability, and is useful as Useful colorants are, for example, dyes used in photosensitive resin compositions for color filters.

The compound may be a compound represented by one of Chemical Formula 4-1 to Chemical Formula 4-4, but is not limited thereto.

[chemical formula 4-4]

The compound according to an embodiment has a molecular structure like that of the compound represented by Chemical Formula 1, and thus can express a more vivid color even in a small amount, and when used as a colorant, can produce a color having excellent characteristics (e.g. brightness, contrast ratio or the like). For example, the dye compound represented by Chemical Formula 1 may have an absorbance maximum (λmax) in a wavelength range of 500 nm to 600 nm.

In general, dyes are the most expensive among the components used in color filters. Accordingly, expensive dyes may need to be used more to achieve desired effects, such as high brightness, high contrast or the like, and thus increase the unit cost of production. However, when the compound according to an embodiment is used as a dye in a color filter, the compound can realize excellent color characteristics such as high brightness, high contrast, and the like even when used in a small amount , and reduce the unit cost of production.

According to another embodiment, a colorant containing a red dye is provided, and the red dye provides a photosensitive resin composition including the compound according to an embodiment.

The compounds according to the examples may function as red dyes (colorants) in photosensitive resin compositions, thereby exhibiting excellent color characteristics.

The photosensitive resin composition may further include a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent. That is, the photosensitive resin composition contains The compound of one embodiment serves as a colorant, and may contain a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

Hereinafter, the components are described in detail.

Colorant

In addition to including the compound according to the embodiment as a red dye, the photosensitive resin composition may further include a pigment as a colorant.

Based on the total amount of the photosensitive resin composition, the content of the colorant may be 1% by weight to 50% by weight, such as 1% by weight to 45% by weight, such as 1% by weight to 40% by weight, such as 1% by weight to 35% by weight %, such as 1% to 30% by weight, such as 1% to 25% by weight, such as 1% to 20% by weight, such as 1% to 15% by weight, such as 1% to 10% by weight, such as 3% by weight % to 10% by weight, such as 5% to 10% by weight, but not limited thereto. When the colorant according to the embodiment is contained within the above range, the color reproduction rate and contrast ratio may be improved.

Pigments may include blue pigments, violet pigments, red pigments, green pigments, yellow pigments, and the like.

Examples of blue pigments may be C.I. Blue Pigment 15:6, C.I. Blue Pigment 15, C.I. Blue Pigment 15:1, C.I. Blue Pigment 15:2, C.I. Blue Pigment 15:3, C.I. Blue Pigment 15 :4, C.I. blue pigment 15:5, C.I. blue pigment 16, C.I. blue pigment 22, C.I. blue pigment 60, C.I. blue pigment 64, C.I. blue pigment 80 or combinations thereof.

Examples of purple pigments can be C.I. Purple pigment 1, C.I. Purple pigment 19, C.I. Purple pigment 23, C.I. Purple pigment 27, C.I. Purple pigment 28, C.I. Purple Pigment 29, C.I. Purple Pigment 30, C.I. Purple Pigment 32, C.I. Purple Pigment 37, C.I. Purple Pigment 40, C.I. Purple Pigment 42, C.I. Purple Pigment 50, or a combination thereof.

Examples of the red pigment may be perylene-based pigments, anthraquinone-based pigments, dianthraquinone-based pigments, azo-based pigments, diazo-based pigments, quinacridone-based pigments, anthracene-based pigments, and the like. Specific examples of red pigments may be perylene pigments, quinacridone pigments, naphthol AS, sicomin pigments, anthraquinones (Sudan I, Sudan II, Sudan III, Sudan R), dianthraquinone compound, bis-azo, benzopyrane (benzopyrane) and the like.

Examples of green pigments may be halogenated phthalocyanine pigments such as C.I. Green Pigment 58, C.I. Green Pigment 59, and the like.

Examples of the yellow pigment may include C.I. Yellow Pigment 139, C.I. Yellow Pigment 138, C.I. Yellow Pigment 150, and the like, and may be used alone or in admixture of two or more.

The pigment may be contained in the photosensitive resin composition in the form of a pigment dispersion.

The pigment dispersion may contain solid pigments, a solvent, and a dispersant in order to uniformly disperse the pigments in the solvent.

Based on the total amount of the pigment dispersion, the solid content of the pigment may be 1% to 20% by weight, such as 8% to 20% by weight, such as 8% to 15% by weight, such as 10% to 20% by weight, For example 10% to 15% by weight.

The dispersant may be a nonionic dispersant, anionic dispersant, cationic dispersant, and the like. Specific examples of the dispersant may be polyglycol and its ester, polyalkylene oxide, polyol ester alkylene oxide addition product, alcohol alkylene oxide addition product, sulfonate, sulfonate, Carboxylate, carboxylate, alkylamine alkylene oxide addition product, alkylamine and the like, and may be used alone or in admixture of two or more.

Commercially available examples of the dispersant may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK manufactured by BYK Co., Ltd. -164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA manufactured by EFKA Chemicals Co. - 47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450 and the like; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse manufactured by Zeneka Co. 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, and the like; or PB711 or PB821 manufactured by Ajinomoto Inc.

The content of the dispersant may be 1% to 20% by weight based on the total weight of the pigment dispersion. When the dispersant is included within the range, the dispersibility of the photosensitive resin composition is improved due to proper viscosity, and thus optical, physical and chemical properties may be maintained when the photosensitive resin composition is applied to products.

Solvents used to form pigment dispersions may be ethylene glycol acetate, ethyl cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like .

binder resin

The binder resin may include an acryl-based binder resin, a cardole-based binder resin, or a combination thereof. For example, the binder resin may be an acryl-based binder resin.

The acryl-based resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer (which can be copolymerized with the first ethylenically unsaturated monomer), and contains at least one acryl Resins based on repeating units.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and examples thereof may be acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or combinations thereof .

Based on the total amount of the acryl-based binder resin, the content of the first ethylenically unsaturated monomer may be 5% to 50% by weight, such as 10% to 40% by weight.

The second ethylenically unsaturated monomer may be: an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene, vinylbenzyl methyl ether, and the like; an unsaturated carboxylic acid ester compound, For example, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, (meth)acrylate ) benzyl acrylate, cyclohexyl (meth)acrylate, phenyl (meth)acrylate and the like; unsaturated aminoalkyl carboxylate compounds such as 2-aminoethyl (meth)acrylate, (meth)acrylate base) 2-dimethylaminoethyl acrylate and the like; vinyl carboxylate compounds such as vinyl acetate, vinyl benzoate and the like; unsaturated glycidyl carboxylate compounds such as (meth)acrylic acid Glycidyl esters and the like; vinyl cyanide compounds such as (meth)acrylonitrile and the like; Unsaturated amide compounds such as (meth)acrylamide and the like; and the like, and may be used alone or in admixture of two or more.

Specific examples of the acryl-based binder resin may be (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid /Benzyl methacrylate/2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, and the like, But not limited thereto, and may be used alone or in admixture of two or more.

The weight average molecular weight of the acryl-based binder resin may be 3,000 g/mol to 150,000 g/mol, for example 5,000 g/mol to 50,000 g/mol, for example 20,000 g/mol to 30,000 g/mol . When the acryl-based binder resin has a weight average molecular weight within the range, the photosensitive resin composition can have excellent physical and chemical properties and appropriate viscosity, maintain appropriate developability and sensitivity, and The color filter exhibits excellent intimate contact properties to the substrate during production.

The acid value of the acryl-based binder resin may be 15 mgKOH/g to 60 mgKOH/g, for example, 20 mgKOH/g to 50 mgKOH/g. When the acryl-based binder resin has an acid value within the range, excellent resolution of pixels can be obtained.

The carbadole-based binder resin may include a repeating unit represented by Chemical Formula 5.

[chemical formula 5]

In chemical formula 5, R ⁶ and R ⁷ are independently a hydrogen atom or a substituted or unsubstituted (meth)acryloxyalkyl group, R ⁸ and R ⁹ are independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl, and Z ¹ is a single bond, O, CO, SO ₂ , CR ¹⁰ R ¹¹ , SiR ¹² R ¹³ (wherein R ¹⁰ to R ¹³ are independently hydrogen atoms or substituted or unsubstituted C1 to C20 alkyl) or one of the linking groups represented by Chemical Formula 6-1 to Chemical Formula 6-11,

[chemical formula 6-3]

In Chemical Formula 6-5, R ^f is a hydrogen atom, an ethyl group, C ₂ H ₄ Cl, C ₂ H ₄ OH, CH ₂ CH═CH ₂ or a phenyl group.

[chemical formula 6-9]

Z ² is an acid dianhydride moiety, and p1 and p2 are independently an integer of 0 to 4.

The carbadole-based binder resin may include a functional group represented by Chemical Formula 7 at at least one terminal.

In Chemical Formula 7, Z ³ may be represented by Chemical Formula 7-1 to Chemical Formula 7-7.

[chemical formula 7-1]

In Chemical Formula 7-1, R ^g and ^Rh are independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group or an ether group.

In Chemical Formula 7-5, R ⁱ is O, S, NH, substituted or unsubstituted C1 to C20 alkylene, C1 to C20 alkylamino or C2 to C20 alkenylamino.

The carbadole-based binder resin can be prepared, for example, by mixing at least two of: a fluorene-containing compound such as 9,9-bis(4-oxiranylmethoxyphenyl)fluorene; an acid anhydride compound, For example, benzene tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, cyclobutane tetracarboxylic dianhydride, perylene tetracarboxylic dianhydride Dianhydride, tetrahydrofurantetracarboxylic dianhydride, and tetrahydrophthalic anhydride; diol compounds, such as ethylene glycol, propylene glycol, and polyethylene glycol; alcohol compounds, such as methanol, ethanol, propanol, n-butanol, cyclic Hexanol and benzyl alcohol; solvent compounds such as propylene glycol methyl ethyl acetate and N-methylpyrrolidone; phosphorus compounds such as triphenylphosphine; and amine or ammonium salt compounds such as tetramethylammonium chloride, Tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, benzyltriethylammonium chloride, and the like.

When the carbadole-based binder resin is used together with the acryl-based binder resin, a photosensitive resin composition having excellent close contact force, high resolution, and high luminous properties can be obtained.

The carbadole-based binder resin may have a weight average molecular weight of 500 g/mol to 50,000 g/mol, for example, 3,000 g/mol to 30,000 g/mol. When the carbadole-based binder resin has a weight average molecular weight within the range, a satisfactory pattern may be formed without residue during production of the color filter and without loss of film thickness during development.

The carbadole-based binder resin may have an acid value of 100 mgKOH/g to 140 mgKOH/g.

Based on the total amount of the photosensitive resin composition, the content of the binder resin may be 1% by weight to 30% by weight, such as 1% by weight to 25% by weight, such as 1% by weight to 20% by weight, such as 1% by weight to 15% by weight. % by weight, such as 1% by weight to 10% by weight, such as 1% by weight to 7% by weight, such as 1% by weight to 5% by weight, but not limited thereto. When the binder resin is included within the range, developability may be improved due to improved crosslinking during production of color filters and excellent surface smoothness may be improved.

photopolymerizable monomer

The photopolymerizable monomer may be a monofunctional or polyfunctional ester of (meth)acrylic acid containing at least one ethylenically unsaturated double bond.

The photopolymerizable monomer has an ethylenically unsaturated double bond, and thus can cause sufficient polymerization during exposure in a pattern forming process, and form a pattern having excellent heat resistance, light resistance, and chemical resistance.

Specific examples of the photopolymerizable compound may be ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate Acrylates, Neopentyl Glycol Di(meth)acrylate, 1,4-Butanediol Di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate ester, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, Dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy resin (meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, Tris(meth)acryloxyethyl phosphate, epoxy novolac (meth)acrylate, and the like.

Commercially available examples of photopolymerizable monomers are as follows. Monofunctional (meth)acrylates may include Aronix M-101 ^® , M-111 ^® , M-114 ^® (Toagosei Chemistry Industry Co., Ltd.); KAYARAD TC-110S ^® , TC-120S ^® (Nippon Kayaku Co., Ltd.); V-158 ^® , V-2311 ^® (Osaka Organic Chemical Ind., Ltd.), and analog. Examples of difunctional (meth)acrylates may include Aronix M-210 ^® , M-240 ^® , M-6200 ^® (Toa Gosei Chemical Industry Co., Ltd.); KAYARAD HDDA ^® , HX-220 ^® , R-604 ^® ( Nippon Kayaku Co., Ltd.); V-260 ^® , V-312 ^® , V-335 HP ^® (Osaka Organic Chemical Industry Co., Ltd.), and the like. Examples of trifunctional (meth)acrylates may include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-710 ^® , M-8030 ^® , M-8060 ^® (Toya Synthetic Chemical Industry Co., Ltd.); KAYARAD TMPTA ^® , DPCA-20 ^® , DPCA-30 ^® , DPCA-60 ^® , DPCA-120 ^® (Nippon Kayaku Co., Ltd.); V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® (Osaka Organic Chemical Industry Co., Ltd.), and the like. These may be used alone or in admixture of two or more.

Photopolymerizable monomers may be treated with acid anhydrides to improve developability.

Based on the total amount of the photosensitive resin composition, the content of the photopolymerizable monomer can be 1% by weight to 15% by weight, such as 1% by weight to 10% by weight, such as 1% by weight to 7% by weight, such as 1% by weight to 5% by weight, but not limited thereto. When the photopolymerizable monomer is contained within the range, it can be sufficiently cured under exposure during the pattern forming process, and thus improves reliability and improves developability with an alkaline developer.

Photopolymerization initiator

The photopolymerization initiator can be an initiator commonly used in photosensitive resin compositions, such as acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, oximes compounds or combinations thereof.

Examples of acetophenone compounds can be 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-tert-butyl Trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-( 4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1- Ketones and the like.

Examples of benzophenone compounds may be benzophenone, benzoyl benzoate, benzoyl methylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4, 4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichloro Benzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.

Examples of thioxanthone compounds may be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone , 2-chlorothioxanthone and the like.

Examples of the benzoin-based compound may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.

Examples of triazine compounds can be 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethyl Oxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2- Biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphthol-yl)-4,6-bis( Trichloromethyl)-triazine, 2-(4-methoxynaphthol-yl)-4,6-bis(trichloromethyl)-triazine, 2-4-bis(trichloromethyl)- 6-helianthyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine and the like.

Examples of oxime compounds can be O-acyl oxime compounds, 2-(o-phthaloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o- Acetyl oxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-oxazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino- 1-Phenylpropan-1-one and the like. Specific examples of O-acyl oxime compounds can be 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl- Phenyl)-butan-1-one, 1-(4-phenylthiophenyl)-butane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylthio Phenyl)-octane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylthiophenyl)-octane-1-one oxime-O-acetate, 1 -(4-Phenylthiophenyl)-butan-1-one oxime-O-acetate and similar thing.

In addition to the above-mentioned compounds, the photopolymerization initiator may further include oxazole compounds, diketone compounds, borate-based compounds, diazo-based compounds, imidazole-based compounds, biimidazole-based compounds, fluorene-based compounds, and the like.

The photopolymerization initiator may be used together with a sensitizer capable of causing a chemical reaction by absorbing light and becoming an excited state and then transferring its energy.

Examples of the sensitizer may be tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, dipentaerythritol tetra-3-mercaptopropionate, and the like.

Based on the total amount of the photosensitive resin composition, the content of the photopolymerization initiator can be 0.01% by weight to 10% by weight, such as 0.01% by weight to 9% by weight, such as 0.01% by weight to 7% by weight, such as 0.01% by weight to 5% by weight, such as 0.01% to 3% by weight, such as 1% to 10% by weight, such as 3% to 10% by weight, but not limited thereto. When the photopolymerization initiator is included within the range, sufficient photopolymerization occurs during exposure in the pattern forming process, excellent reliability can be achieved, heat resistance, light resistance, and chemical resistance, resolution, and heat resistance of the pattern can be improved. rate and close contact properties, and can prevent light transmittance from decreasing due to non-reactive initiators.

solvent

The solvent may be a material having compatibility with, but not reacting with, the (dye) compound, the pigment, the binder resin, the photopolymerizable monomer, and the photopolymerization initiator according to an embodiment.

Examples of solvents may include: alcohols such as methanol, ethanol, and the like; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran, and the like analogues; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and the like; ethylene glycol acetates such as methyl glycol acetate, ethyl glycol acetate, diethyl Ethyl glycol acetate and the like; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl Ethers, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and the like; propylene glycol alkyl ether acetates, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, and the like; aromatic hydrocarbons , such as toluene, xylene, and the like; ketones, such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl n-acetone, methyl n-butanone, methyl n-Pentanone, 2-heptanone, and the like; alkyl esters of saturated aliphatic monocarboxylates, such as ethyl acetate, n-butyl acetate, isobutyl acetate, and the like; lactate esters, such as methyl lactate, lactic acid Ethyl esters and the like; Alkyl oxyacetates such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate and the like; Alkyl oxyacetates such as methyl methoxyacetate , ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate and the like; alkyl 3-oxypropionates such as methyl 3-oxypropionate esters, ethyl 3-oxypropionate, and the like; alkyl 3-alkoxypropionates such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3-ethoxy ethyl 2-oxypropionate, methyl 3-ethoxypropionate and the like; alkyl 2-oxypropionate such as methyl 2-oxypropionate, ethyl 2-oxypropionate, 2- Propyl oxypropionate and the like; alkyl 2-alkoxypropionate such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate esters, methyl 2-ethoxypropionate, and the like; 2-oxy-2-methylpropionate esters such as methyl 2-oxy-2-methylpropionate, Ethyl methylpropionate and analogues; alkyl 2-alkoxy-2-methylpropionate Alkyl monooxymonocarboxylates, such as methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, and the like; esters, such as ethylpropionate 2-Hydroxylate, 2-hydroxy-2-methyl ethylpropionate, hydroxyethylacetate, 2-hydroxy-3-methylmethylbutyrate, and the like; ketoesters such as ethylpyruvate and the like. In addition, high-boiling solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformaniline, N-methylacetamide, N,N-di Methylacetamide, N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1- Nonanol, Benzyl Alcohol, Benzyl Acetate, Ethyl Benzoate, Diethyl Oxalate, Diethyl Maleate, Gamma-Butyrolactone, Ethylene Carbonate, Propylene Carbonate, Phenyl Glycol Ethyl alcohol acetate and the like.

In consideration of mutual solubility and reactivity, ketones such as cyclohexanone and the like; glycol alkyl ether acetates such as ethyl glycol ethyl acetate and the like; esters such as ethyl propionic acid 2-Hydroxy esters and the like; carbitols such as diethylene glycol monomethyl ether and the like; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate.

Based on the total amount of the photosensitive resin composition, the remaining amount of the solvent is, for example, 20% by weight to 90% by weight. When the solvent within the above range is included, the photosensitive resin composition may have an appropriate viscosity, thereby improving the coating properties of the color filter.

other additives

The photosensitive resin composition may further contain other additives, such as malonic acid, 3-amino-1,2-propanediol, carboxyl, reactive substituents (such as methacryl, isocyanate, epoxy and the like) ) silane coupling agent, leveling agent, fluorine Surfactant-like agents, radical polymerization initiators, and the like, in order to prevent stains or spots during coating, adjust leveling characteristics, or prevent pattern residue due to non-development.

Examples of silane coupling agents can be trimethoxysilyl benzoic acid, γ-methacrylpropoxytrimethoxysilane, vinyltriacetyloxysilane, vinyltrimethoxysilane, γ-isocyanate Propyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane and the like, and these may be used alone or Used as a mixture of two or more.

Based on 100 parts by weight of the photosensitive resin composition, the content of the silane coupling agent may be 0.01 to 10 parts by weight. When the silane coupling agent within the above range is included, adhesion and storage can be improved.

The photosensitive resin composition may further include an epoxy compound to improve the intimate contact property with the substrate.

Examples of epoxy compounds may be phenol novolak epoxy compounds, tetramethylbiphenyl epoxy compounds, bisphenol A epoxy compounds, alicyclic epoxy compounds, or combinations thereof.

Based on 100 parts by weight of the photosensitive resin composition, the content of the epoxy compound may be 0.01 to 20 parts by weight, such as 0.1 to 10 parts by weight. When the epoxy compound within the range is contained, intimate contact properties, storage properties, and the like may be improved.

In addition, the photosensitive resin composition may further include a surfactant in order to improve coating properties and prevent generation of defects when necessary.

The surfactant may contain a fluorosurfactant, and examples of the fluorosurfactant may be F-482, F-484, F-478, F-554, and the like from DIC Co., Ltd. things, but not limited to this.

Based on 100 parts by weight of the photosensitive resin composition, the content of the surfactant may be 0.001 to 5 parts by weight. When the surfactant is contained within the range, coating uniformity is ensured, no stain is found, and the wetting property of the glass substrate is excellent.

In addition, the photosensitive resin composition may further contain predetermined amounts of other additives such as oxidation inhibitors, stabilizers, and the like unless the properties deteriorate.

According to another embodiment, there is provided a photosensitive resin layer produced using the photosensitive resin composition according to an embodiment.

According to another embodiment, there is provided a color filter produced using the photosensitive resin composition according to the embodiment.

The pattern forming process in the color filter is as follows.

The process includes: coating a photosensitive resin composition according to an embodiment on a support substrate by spin coating, slit coating, inkjet printing, and the like; drying the coated positive photosensitive resin composition to form a photosensitive resin composition layer; exposing the positive photosensitive resin composition layer; developing the exposed positive photosensitive resin composition layer in an alkaline aqueous solution to obtain a photosensitive resin layer; and heat-treating the photosensitive resin layer. Conditions for the patterning process are well known in the related art and will not be described in detail in this specification.

According to another embodiment, there is provided a display device including the color filter according to the embodiment. The display device may be, for example, a liquid crystal display (LCD).

Hereinafter, preferred embodiments of the present invention will be described. However, these examples should not be construed as limiting the scope of the invention in any sense.

Synthesis Example: Synthesis of Compounds

Synthesis Example 1: Synthesis of Compounds Represented by Chemical Formula 4-1

Add 10 equivalents of 2-propanol and 2 equivalents of 2-(ethylamino)ethanol to 1 equivalent of 3',6'-dichlorospiro[3H-2,1-benzoxathiol-3,9' -[9H]xanthene]-1,1-dioxide, and then stirred at room temperature for 3 hours. After stirring, 2 equivalents of 2,6-dimethylaniline were added thereto, and then stirred at 30° C. for 3 hours. A precipitate was obtained by using diethyl ether, and then dried to obtain Intermediate 1. 0.5 equivalents of hexamethylene diisocyanate, dibutyl laurate, and methylene chloride were added to Intermediate 1, and then reacted therewith at 40°C to obtain Intermediate 2. Intermediate 2 was reacted with methacryloyl chloride in a dichloromethane solvent to synthesize a compound represented by Chemical Formula 4-1.

Maldi-tof MS: (1,477.75) m/z

Synthesis Example 2: Synthesis of Compounds Represented by Chemical Formula 4-2

The compound represented by Chemical Formula 4-2 was synthesized according to the same method as Synthesis Example 1 except that 2,4-dimethylaniline was used instead of 2,6-dimethylaniline.

[chemical formula 4-2]

Maldi-tof MS: (1,477.75) m/z

Synthesis Example 3: Synthesis of Compounds Represented by Chemical Formula 4-3

The compound represented by Chemical Formula 4-3 was synthesized according to the same method as Synthesis Example 1, except that isophorone diisocyanate was used instead of hexamethylene diisocyanate.

Maldi-tof MS: (1,517.82) m/z

Synthesis Example 4: Synthesis of Compounds Represented by Chemical Formula 4-4

The compound represented by Chemical Formula 4-4 was synthesized according to the same method as Synthesis Example 1, except that m-xylene diisocyanate was used instead of hexamethylene diisocyanate.

[chemical formula 4-4]

Maldi-tof MS: (1,497.74) m/z

Comparative Synthesis Example 1: Synthesis of Compounds Represented by Chemical Formula X

Add 10 equivalents of 2-propanol and 2 equivalents of 2-(ethylamino)ethanol to 1 equivalent of 3',6'-dichlorospiro[3H-2,1-benzoxathiol-3,9' -[9H]xanthene]-1,1-dioxide, and then stirred at room temperature for 3 hours. A precipitate was obtained by using diethyl ether, and then dried to obtain Intermediate 1. 0.5 equivalents of N,N'-dimethyl-1,6-hexanediamine and NMP were added to Intermediate 1, and then reacted at 120°C for one day to obtain Intermediate 2. Intermediate 2 was reacted with methacryloyl chloride in a dichloromethane solvent to synthesize a compound represented by Chemical Formula X.

Maldi-tof MS: (1,151.40) m/z

Comparative Synthesis Example 2: Synthesis of Compounds Represented by Chemical Formula Y

Add 10 volumes of 2-propanol and 2 equivalents of 2-(ethylamino)ethanol to 1 equivalent of 3',6'-dichlorospiro[3H-2,1-benzoxathiol-3,9' -[9H]xanthene]-1,1-dioxide , and then stirred at 50 °C for 3 hours. A precipitate was obtained by using diethyl ether, and then dried to obtain Intermediate 1. 0.5 equivalents of hexamethylene diisocyanate, dibutyl laurate, and methylene chloride were added to Intermediate 1, and then reacted at 40°C to obtain Intermediate 2. Intermediate 2 was reacted with methacryloyl chloride in dichloromethane solvent to synthesize compound Y.

Maldi-tof MS: (1,325.56) m/z

Example: Synthesis of photosensitive resin composition

Example 1 to Example 4 and Comparative Example 1 and Comparative Example 2

The photopolymerization initiator was put into a solvent according to the components shown in Table 1, and then stirred at room temperature for 1 hour and dissolved therein. Subsequently, a binder resin and a photopolymerizable monomer were added thereto, and then stirred at room temperature for 1 hour. Then, other additives were added thereto, and then stirred at room temperature for 1 hour. Subsequently, the compounds according to Synthesis Example 1 to Synthesis Example 4 and Comparative Synthesis Example 1 and Comparative Synthesis Example 2 were added thereto (or together with a red pigment), and then stirred at room temperature for 2 hours, and the solution was filtered three times to remove Impurities were removed, thereby preparing photosensitive resin compositions according to Example 1 to Example 4 and Comparative Example 1 and Comparative Example 2. A photosensitive resin composition was prepared by using the following components.

(A) Binder resin

Acryl-based binder resin (RY-25, Showadenko K.K.)

(B) Photopolymerizable monomer

DPHA (Nippon KAYAKU)

(C) Photopolymerization initiator

SPI-03 (Samyang Corp.)

(D) Colorant

(D-1) Compounds according to Synthesis Example 1

(D-2) Compounds according to Synthesis Example 2

(D-3) Compounds according to Synthesis Example 3

(D-4) Compounds according to Synthesis Example 4

(D-5) according to the compound of Comparative Synthesis Example 1

(D-6) according to the compound of comparative synthesis example 2

(D-7) C.I. Red Pigment 254 (Sanyo Color Works Ltd.)

(D-8) C.I. Red Pigment 177 (Sanyo Pigment Co., Ltd.)

(E) solvent

Propylene glycol monomethyl acetate (PGMEA, Sigma-Aldrich Co.,Ltd.)

(F) Other additives

Fluorosurfactant (F-554, DIC Corporation)

Evaluation 1: Evaluation of Luminescence Characteristics

The photosensitive resin compositions of Examples 1 to 4 and Comparative Examples 1 and 2 were coated to have a thickness of 1 μm to 3 μm, respectively, on a 1 mm thick degreased and washed glass substrate, and then heated at 90° C. The plate was dried for 2 minutes to obtain a film. Subsequently, a high pressure mercury lamp with a dominant wavelength of 365 nm was used to fully expose the film at 60 mJ/cm2. Next, the film was dried in a forced convection drying oven at 230° C. for 20 minutes to obtain samples with the same thickness. The brightness of the pixel layer was measured by using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the results are shown in Table 2.

Evaluation 2: Evaluation of Durability

Color filter samples formed from the photosensitive resin compositions according to Examples 1 to 4 and Comparative Examples 1 and 2 were used for patterning, and then heated at 230° C. The pattern was heat-treated in an oven for 30 minutes to evaluate durability, and a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.) was used to measure its color change and absorbance change. Next, the results are shown in Table 2.

Referring to Table 2, compared with the compositions of Comparative Example 1 and Comparative Example 2 that do not contain the compound of the present invention, the photosensitive resin compositions of Examples 1 to 4 containing the compound (red dye) according to one embodiment exhibited excellent Excellent durability (such as heat resistance, chemical resistance and the like) and excellent color characteristics (such as brightness and the like).

In the above, some exemplary embodiments of the present invention have been described and illustrated, however, it is obvious to those skilled in the art that the present invention is not limited to the exemplary embodiments as described, and can be modified without departing from the present invention. Various modifications and transformations are made within the spirit and scope of the case. Accordingly, the modified or converted exemplary embodiments thus may not be understood from the technical idea and aspect of the present invention alone, and the modified exemplary embodiments are within the scope of the claims of the present invention.

none.

Claims (16)

A dye compound represented by Chemical Formula 1:

Wherein, in Chemical Formula 1, R ¹ is substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heteroaryl or a combination thereof, R ² , R ⁴ and R ⁵ are independently is substituted or unsubstituted C1 to C20 alkylene, substituted or unsubstituted C3 to C20 cycloalkylene, substituted or unsubstituted C6 to C20 arylylene, substituted or unsubstituted C2 to C20 heteroaryl or a combination thereof, and R ³ is hydrogen, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C2 to C20 heterocyclic group or a combination thereof. The dye compound as claimed in claim 1, wherein: R ² and R ⁴ are independently substituted or unsubstituted C1 to C20 alkylene, or substituted or unsubstituted C3 to C20 cycloalkylene, And R ⁵ is substituted or unsubstituted C1 to C20 alkylene, substituted or unsubstituted C3 to C20 cycloalkylene, substituted or unsubstituted C6 to C20 arylylene, substituted or Unsubstituted C2 to C20 heteroaryl or a combination thereof. The dye compound as claimed in claim 1, wherein: R ¹ is substituted or unsubstituted C6 to C20 aryl, and R ⁵ is substituted or unsubstituted C1 to C20 alkylene, substituted or unsubstituted Substituted C6 to C20 arylenyl or a combination thereof. The dye compound as described in claim 1, wherein R ¹ is represented by chemical formula 2:

Wherein, in Chemical Formula 2, R ^a to R ^e are independently hydrogen, or substituted or unsubstituted C1 to C5 alkyl, and "*" represents a connection point. The dye compound as described in claim 1, wherein R ⁵ is represented by chemical formula 3:

Wherein, in Chemical Formula 3, L ^a and L ^b are independently a single bond, or a substituted or unsubstituted C1 to C5 alkylene group, and "*" represents a connection point. The dye compound as claimed in claim 1, wherein the dye compound is a compound represented by one of Chemical Formula 4-1 to Chemical Formula 4-4,

[chemical formula 4-4]

The dye compound according to claim 1, wherein the dye compound represented by Chemical Formula 1 has a maximum absorbance in a wavelength range of 500 nm to 600 nm. A photosensitive resin composition, comprising: a coloring agent containing a red dye, and the red dye includes the dye compound described in any one of claim 1 to claim 7. The photosensitive resin composition according to claim 8, wherein the photosensitive resin composition further includes a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent. The photosensitive resin composition according to claim 9, wherein the binder resin comprises an acryl-based binder resin, a carbadole-based binder resin, or a combination thereof. The photosensitive resin composition according to claim 8, wherein the colorant further includes a pigment. The photosensitive resin composition as described in Claim 9, wherein the photosensitive resin composition includes in terms of the total amount of the photosensitive resin composition; 1% to 50% by weight of the colorant; 1% to 30% by weight of the binder resin; 1% to 15% by weight of the photopolymerizable monomer; 0.01% to 10% by weight of the photopolymerization initiator; and the remaining amount of the solvent. The photosensitive resin composition as described in Claim 9, wherein the photosensitive resin composition further includes malonic acid, 3-amino-1,2-propanediol, vinyl or (meth)acryloxy Silane coupling agent, leveling agent, surfactant, radical polymerization initiator or combination thereof. A photosensitive resin layer produced using the photosensitive resin composition described in Claim 8. A color filter produced using the photosensitive resin composition described in claim 8. A display device, comprising the color filter as claimed in claim 15.